Nucleosides of 1,2,3-triazole substituted at position 4 of the aglycon are of interest as structural isomers of the broad spectrum antiviral nucleoside 1-.beta.-D-ribofuranosyl-1,2,4-triazole-3-carboxamide and the analogs thereof described in our copending U.S. application Ser. No. 240,252 filed Mar. 31, 1972, now U.S. Pat. No. 3,798,209. The disclosure of that application is incorporated herein to illuminate the background of this invention. The cycloaddition of various glycosyl azides with substituted acetylenes has provided numerous examples of 1 (3)-glycosyl-1,2,3-triazoles, eg: ##SPC1##
Such reactions are described, eg., in F. Michael et al. Chem. Ber. 90, 1595 (1957); J. Baddiley et al. J. Chem. Soc., 1951 (1958); Ibid. 3606; G. Garcia-Munoz et al., J. Heterocyclic Chem. 5, 699 (1968); Ibid. 6, 639 (1969); G. Alonso et al., ibid., 7, 1269 (1970); H. El Khadem et al. Cabohyd. Res., 16, 409 (1971); R. E. Harmon et al. J. Org. Chem. 36, 2553 (1971) and R. E. Harmon et al., J. Chem. Soc., Chem. Commun., 296 (1971), although in none of the foregoing publications is biological activity reported for the compounds dealt with. However, isomeric 2-glycosyl-1,2,3-triazoles (ie, compounds of structure ##SPC2##
Are not accessible from azido sugars. We have now prepared a number of novel 1(2)-ribofuranosyl-1,2,3-triazoles by fusion of 1,2,3-triazole or 4-substituted 1,2,3-triazole with tetra-0-acyl blocked .beta.-D-ribofuranose. Compounds prepared according to this invention have exhibited significant antimicrobial activity, variously against Pseudomonas aeroginosa, Staphylococcus aureas, Escherichia coli, Streptococcus faecalis, Bacillus subtilis, Aspergillus niger and Candida albicans. Preferred compounds are those of structure ##SPC3##
Wherein R' is as defined above and wherein R is hydrogen or C.sub.1 - C.sub.18, preferably C.sub.1 - C.sub.4, acyl.